When I was in high school, I drove west to Madison (from Milwaukee) for the day to shop around State Street and visit some friends who’d gone to college there the previous there.

Back in high school, I did a fair amount of record shopping and also had a decent number of shirts with my favorite artists on them.

One of my favorites was (and still is) The The, Matt Johnson’s band. Their second album, Infected, had come out in 1986, and the album cover looks like this:

A little twisted, but interesting and certainly not controversial.

While shopping, I saw a The The shirt in my size and was pretty excited to get a unique shirt with this fairly unknown band’s artwork. So I picked it up, hung out a bit more and headed home.

When I got home, my parents asked me what I had gotten. Excitedly, I pulled the shirt out of the bag and showed them.

Unfortunately, I had never really looked at it before I purchased it, so when I unfolded it for them, we were all seeing it for the first time together. This is what it looked like (WARNING: this is inappropriate for kids, so you’ll have to scroll a bit to see it):

This remains one of the most embarrassing moments of my teenage career. Learned a valuable lesson on that one.

Naturally, I never wore it and took it back as soon as I could.